Abstract
α,β-Unsaturated acetylenic γ-hydroxyketones have been shown to react with ethyl acetoacetate in a Michael-addition fashion and subsequently undergo cyclization followed by dehydration to give substituted furans with a predictable regiospecificity. The yields were good to excellent. A mechanism for the transformation is proposed, and this mechanism explains why furan formation does not take place when the same unsaturated ketones are treated with α-methylated acetoacetate and diethyl malonate.
Original language | English |
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Journal | Synthetic Communications |
Volume | 43 |
Issue number | 21 |
Pages (from-to) | 2898-2905 |
ISSN | 0039-7911 |
DOIs | |
Publication status | Published - 2013 |
Externally published | Yes |
Bibliographical note
Supplementary materials are available for this article. Go to the publisher’s online edition of Synthetic Communications1 for the following free supplemental resource: Full experimental and spectral details.Keywords
- Conjugated acetylenic ketones
- Ketoesters
- Propargylic alcohols